Diverse Uses of the Reaction of Frustrated Lewis Pair (FLP) with Hydrogen

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(48), С. 20002 - 20014

Опубликована: Ноя. 17, 2021

The articulation of the notion "frustrated Lewis pairs" (FLPs) emerged from discovery that H2 can be reversibly activated by combinations sterically encumbered main group acids and bases. This has prompted numerous studies focused on various perturbations acid/base applications to organic reductions. Perspective focuses new directions developments are emerging this FLP chemistry involving hydrogen. Three areas discussed including approaches reductions, reductions small molecules, advances in heterogeneous systems. These foci serve illustrate despite having its roots chemistry, simple concept FLPs is being applied across discipline.

Язык: Английский

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Frustrated Lewis pair chemistry of alkynes

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2375 - 2396

Опубликована: Янв. 1, 2024

This review is focused on the chemistry of frustrated Lewis pairs (FLPs) with alkynes and surveys range stoichiometric catalytic reactions enabled by this concept.

Язык: Английский

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Acid-catalyzed conversion of sesamolin to sesamol: Kinetics and reaction mechanism based on density functional theory

Food Chemistry, Год журнала: 2025, Номер 472, С. 142972 - 142972

Опубликована: Янв. 20, 2025

Язык: Английский

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Asymmetric Reduction of Quinolines: A Competition between Enantioselective Transfer Hydrogenation and Racemic Borane Catalysis

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(5), С. 3335 - 3339

Опубликована: Фев. 17, 2023

A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines with regenerable dihydrophenanthridine derived by a borane-catalyzed phenanthridine under H2 has been successfully realized. Despite the competition racemic pathway, variety tetrahydroquinolines were furnished in high yields up to 91% ee.

Язык: Английский

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Origin of Stereoselectivity in FLP-Catalyzed Asymmetric Hydrogenation of Imines

ACS Catalysis, Год журнала: 2020, Номер 10(23), С. 14290 - 14301

Опубликована: Ноя. 23, 2020

Development of metal-free strategies for stereoselective hydrogenation unsaturated substrates is particular interest in asymmetric synthesis. The emerging chemistry frustrated Lewis pairs offers a promising approach along this line as demonstrated by recent achievements. However, the stereocontrol elements these reactions are not clearly recognized thus far. Herein, we analyze origin stereoinduction direct imines catalyzed set chiral boranes. We use tools computational to describe elementary steps catalytic cycle, and pay special attention stereoselectivity-determining hydride transfer process. enantioselectivities predicted applied very good agreement with previous experimental observations. find that stereoselectivity governed thermodynamically less favored conformer borohydride intermediate experimentally observed form. most transition states stabilized specific aryl–aryl alkyl–aryl noncovalent interactions, which play an important role stereoinduction. This insight exploited proposing additional borane variants improve enantioselectivity, could be

Язык: Английский

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Recent Advances in Asymmetric Catalysis Using p‐Block Elements

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(9)

Опубликована: Дек. 1, 2023

The development of new methods for enantioselective reactions that generate stereogenic centres within molecules are a cornerstone organic synthesis. Typically, metal catalysts bearing chiral ligands as well organocatalysts have been employed the synthesis compounds. In this review, we highlight recent advances in main group catalysis using p-block elements (boron, aluminium, phosphorus, bismuth) complementary and sustainable approach to molecules. Several these benefit terms high abundance, low toxicity, selectivity, excellent reactivity. This minireview summarises utilisation element asymmetric value-added

Язык: Английский

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B(C₆F₅)₃-Catalyzed site-selective N¹-alkylation of benzotriazoles with diazoalkanes

Chemical Communications, Год журнала: 2021, Номер 57(63), С. 7758 - 7761

Опубликована: Янв. 1, 2021

The site-selective N¹-alkylation of benzotriazoles with diazoalkanes is achieved using 10 mol% B(C₆F₅)₃ as a catalyst.

Язык: Английский

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FLP-CO2 adducts: Convenient sources of frustrated Lewis pairs for stoichiometric and catalytic chemistry

Dalton Transactions, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

[ t Bu 3 PCO 2 B(C 6 F 5 ) ] 1 and [TMPH][C H Me 4 NCO 7 act as FLP precursors react with , disulfides, alkynes, silanes phenols. While is a catalyst precursor for the hydrogenation hydrosilylation of selected substrates.

Язык: Английский

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Rare-earth mediated dihydrogen activation and catalytic hydrogenation

Journal of Rare Earths, Год журнала: 2021, Номер 39(9), С. 1017 - 1023

Опубликована: Янв. 9, 2021

Язык: Английский

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Chiral Dienes: From Ligands to FLP Catalysts

Chinese Journal of Chemistry, Год журнала: 2021, Номер 40(9), С. 1109 - 1116

Опубликована: Дек. 27, 2021

Comprehensive Summary Olefins are very easily accessible compounds which both popular substrates in synthetic chemistry and good ligands the organometallic complexes. This dual character makes olefins a rich source of chiral catalysts for asymmetric catalysis. Herein, we will briefly summarize our studies on development diene transition‐metal catalyzed reactions FLP metal‐free hydrogenations hydrosilylations. Several acyclic as well P/olefin S/olefin hybrid were developed Rh or Pd‐catalyzed reactions. With these hand, further put forward novel strategy acquiring via situ hydroboration dienes with Piers’ borane. These proved to be highly effective hydrosilylations imines, silyl enol ethers, ketones, aromatic N ‐heterocycles. What is most favorite original your research group? The precursors catalysts. How do you get into this specific field? Could please share some experiences readers? When I started my independent 2008, belong one ligand type. We got field thought simpler better. experience led us step important personality scientific research? Courage persistence doing something unique. hobbies? Walking playing cards. keep balance between family? Life not only research, but also family. You believe it, there. journal(s)? My journal Organic Letters , authors can publish their work rapidly readers browse progress organic comprehensively.

Язык: Английский

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